60-79-7 Usage
Chemical Properties
solid
Originator
Ergotrate,Lilly
Uses
Ergonovine is a water-soluble lysergic acidderivative that occurs in ergot. It is used as anoxytocic agent. Its maleate derivative is usedin the treatment of postpartum hemorrhage.
Definition
ChEBI: A monocarboxylic acid amide that is lysergamide in which one of the hydrogens attached to the amide nitrogen is substituted by a 1-hydroxypropan-2-yl group (S-configuration). An ergot alkaloid that has a particularly powerful action on th
uterus, its maleate (and formerly tartrate) salt is used in the active management of the third stage of labour, and to prevent or treat postpartum of postabortal haemorrhage caused by uterine atony: by maintaining uterine contraction and tone, blood vesse
s in the uterine wall are compressed and blood flow reduced.
Manufacturing Process
A solution of the mixed anhydride of lysergic acid and trifluoroacetic acid is
prepared from 530 mg of d-lysergic acid and 930 mg of trifluoroacetic
anhydride in 30 ml of acetonitrile at -20°C. The mixture is allowed to stand at
-20°C for about 1.5 hours during which time the suspended material
dissolves, and the d-lyserginic acid is converted to the mixed anhydride of
liserginic and trifluoroacetic acids. The mixed anhydride can be separated as
an oil by evaporating the solvent in vacuo at a temperature about 0°C. The
solution containing the mixed anhydride is added to a solution of 300 mg of L-
(+)-2-aminopropan-1-ol, and 640 mg of triethylamine in 15 ml of acetonitrile,
the triethylamine being employed to displace any L-(+)-2-aminopropan-1-ol
from adducts with acid components of the reaction mixture. After 15 minutes
of standing at room temperature, the reaction mixture is filtered, and the
crystalline material thus obtained is washed with acetonitrile and dried in air.
This material is substantially pure d-lysergic acid. The filtrate which contains
the desired reaction product is evaporated to dryness in vacuo. The residue is
treated with chloroform and water. The chloroform layer is separated, and the
aqueous layer is extracted with 4x50 ml portions of chloroform. The combined
chloroform extracts washed 4x50 ml portions of cold water in order to remove
the residual amounts of amine salts, dried over sodium sulfate and the
chloroform is evaporated yielding a crystalline material, which separates when
the volume of residual solution is decreased to about 2 ml. The solution is
chilled, thereby, causing further crystalline material to separate from solution.
The crystalline material is substantially pure ergonovine. The crystalline
ergonovine is removed from the solution by filtration, is washed with cold
chloroform and dried. MP: 155°-156°C. Paper chromatography shows that this
compound is identical with authentic ergonovine produced from crude ergot.The mother liquors and chloroform washes from the above crystallization of
ergonovine are combined, and the solvents are evaporated in vacuo. The
residue containing ergonovinine (the "iso" form of ergonovine) is dissolved in
2 ml of ethyl acetate. From this solution crystalline ergonovinine precipitates
almost immediately. The crystals are separated by filtration and dried. A
sample melts at about 188-190°C. The ergonovinine can be isomerized to
ergonovine with alkali for example by employing the method of Stoll and
Hofmann, Helvetica Chimica Acta 26, 944 (1943).The ethyl acetate mother liquor from the preceding isolation of ergonovinine is
evaporated to dryness in vacuo and the residue (the mixture of 1-
aminopropan-2-ol esters of d-lysergic acid and of d-iso-lysergic acid) is
dissolved in 2 ml of ethanol. 0.4 ml of 4 N potassium hydroxide solution in
50% aqueous ethanol are then added, and the resulting mixture is allowed to
stand at room temperature in the dark for about two hours. This treatment of
the aminopropanol esters of d-lysergic acid and d-isolysergic acid with base
rearranges them to the propanol amides of d-lysergic acid and d-iso-lysergic
acid, which are ergonovine and ergonovinine, respectively. Solid carbon
dioxide is added to the reaction mixture in order to neutralize the potassium
hydroxide. The solvents are then removed in vacuo and the residue ofergonovine and ergonovinine is separated into its components by a
chromatogrophy on the basic alumina. Two blue fluorescing zone appear on
the alumina column and could light isolate. The mixture (3:1) of benzene and
chloroform is used as eluent.
Hazard
Extremely toxic; vaso-constrictor; central nervous system stimulant; adrenergic blocking
compound.
Health Hazard
The toxicity of ergonovine is low to moderate.The toxic symptoms include excitability,respiratory depression, cyanosis, and convulsions.The intravenous LD50 value in mice is144 mg/kg.
Check Digit Verification of cas no
The CAS Registry Mumber 60-79-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 0 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 60-79:
(4*6)+(3*0)+(2*7)+(1*9)=47
47 % 10 = 7
So 60-79-7 is a valid CAS Registry Number.
InChI:InChI=1/C19H23N3O2/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/t11-,13+,17+/m0/s1
60-79-7Relevant articles and documents
Crystallographic and NMR investigation of ergometrine and methylergometrine, two alkaloids from claviceps purpurea
Ciceri, Samuele,Elahi, Shahrzad Reza,Ferraboschi, Patrizia,Grisenti, Paride,Meneghetti, Fiorella,Mori, Matteo
, (2020/01/28)
Ergometrine and methylergometrine are two alkaloids that are used as maleate salts for the prevention and control of postpartum hemorrhage. Although the two molecules have been known for a long time, few and discordant crystallographic and NMR spectroscopic data are available in the literature. With the aim of providing more conclusive data, we performed a careful NMR study for the complete assignment of the 1H, 13C, and 15N NMR signals of ergometrine, methylergometrine, and their maleate salts. This information allowed for a better definition of their conformational equilibria. In addition, the stereochemistry and the intermolecular interactions in the solid state of the two maleate salts were deeply investigated by means of single-crystal X-ray diffraction, showing the capability of these derivatives to act as both hydrogen-bond donors and acceptors, and evidencing a correlation between the number of intermolecular interactions and their different solubility.
Preparation method of ergonovine
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Paragraph 0054-0062, (2017/08/27)
The invention particularly provides a method for preparing racemized ergotic acid by using fermented wastes. The method comprises the following operation steps: firstly, taking wastes obtained by fermenting claviceps purpurea, and generating a hydrolysis reaction in alcohol solvents in the presence of strong base; secondly, removing the alcohol solvents from a hydrolysis reaction product, then acidifying until a pH value is 3.5 to 4.0, and extracting a separated solid matter 1 by using a mixed solution of methanol and ammonia water; thirdly, removing a solvent from an extracting solution, and beating an obtained solid matter 2 by using water and alcohol solvents of C1 to C5 in sequence, thus obtaining the racemized ergotic acid. The invention also provides the method for preparing ergonovine by using the fermented wastes. The method disclosed by the invention is simple and low in cost; no complex splitting process is needed, the reaction is easy to operate, large-scale production is easy, and recycling of the wastes is realized; after the prepared ergonovine is only beaten and purified, the optical purity is 98 percent or above; the ergonovine is suitable for industrial production.
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